Hydrochloric Acid → HCID 68090910, compound

HRID 539020Notes

Reaction equation

HRID 539020 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[N:14][N:15]3[CH:20]=[CH:19][C:18]([N:21]4[C@@H:25]([CH:26]([CH3:28])[CH3:27])[CH2:24][N:23]([CH2:29][CH:30]5[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]5)[C:22]4=[O:36])=[N:17][C:16]=23)=[CH:8][CH:7]=1.C=O.[BH3-][C:40]#N.[Na+].C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:55].Cl.Cl>CC#N.ClCCl.O1CCOCC1>[ClH:55].[ClH:55].[NH:3]1[CH:4]=[CH:5][N:1]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[N:14][N:15]3[CH:20]=[CH:19][C:18]([N:21]4[C@@H:25]([CH:26]([CH3:28])[CH3:27])[CH2:24][N:23]([CH2:29][CH:30]5[CH2:35][CH2:34][N:33]([CH3:40])[CH2:32][CH2:31]5)[C:22]4=[O:36])=[N:17][C:16]=23)=[CH:8][CH:7]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 67034108HCID 67034108, compound

Product 1

HCID 68090910HCID 68090910, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (S)-3-(3-(4-(1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyl-1-(piperidin-4-ylmethyl)imidazolidin-2-one (Example 21; 2.1 mg, 0.0043 mmol) and formaldehyde (37% aqueous solution, 0.003 mL, 0.04 mmol) in MeCN (0.5 mL) was added NaBH3CN (0.8 mg, 0.42 mmol), and the reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was diluted with dichloromethane, washed with saturated aqueous NaHCO3 solution and brine, dried and concentrated. The residue was purified by column chromatography (dichloromethane:7N ammonia in MeOH, 10:1) to give the free base, which was converted to dihydrochloride salt by treatment with 4N HCl in dioxane. LCMS (APCI+) m/z 499.8 [M+H]+.

Workup

  1. washwashed with saturated aqueous NaHCO3 solution and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (dichloromethane:7N ammonia in MeOH, 10:1)
  5. customto give the free base, which

Sources & evidence

ORD record
ord-73e832cf0b5a47448aaa6b5aa202f86e
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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